N-Methylbutylamine → 6-bromo-4-(butylmethylamino)-3-propyl-2H-1-benzopyran-2-one

HRID 1636434Notes

Reaction equation

HRID 1636434 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([CH2:12][CH2:13][CH3:14])=[C:7](Cl)[C:6]=2[CH:16]=1.[CH3:17][NH:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([CH2:12][CH2:13][CH3:14])=[C:7]([N:18]([CH2:19][CH2:20][CH2:21][CH3:22])[CH3:17])[C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 193516286-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one

Product 1

HCID 193516446-bromo-4-(butylmethylamino)-3-propyl-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one (0.4 g) and N-methylbutylamine (3 ml) in dimethylformamide (2 ml) was heated under reflux for 30 minutes and then allowed to cool overnight. Evaporation followed by column chromatography yielded 6-bromo-4-(butylmethylamino)-3-propyl-2H-1-benzopyran-2-one, as an oil. (compound 18).

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureto cool overnight
  3. customEvaporation

Sources & evidence

ORD record
ord-c8df5447ccbe4b21b9092117527e3403
Source dataset
uspto-grants-2000_03
Patent number
US06034121

Reaction notes

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